Ammonia → HCID 10194183, compound

HRID 352658Notes

Reaction equation

HRID 352658 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:10]=2)[N:5]=[CH:4][N:3]1[CH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=1.C(Cl)(=O)C(Cl)=O.[NH3:37]>ClCCl.CN(C=O)C.O1CCOCC1>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:10]=2)[N:5]=[CH:4][N:3]1[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([NH2:37])=[O:28])=[CH:29][CH:30]=1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 10237571HCID 10237571, compound

Product 1

HCID 10194183HCID 10194183, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

0.1 g (0.254 mmol) of the compound of Example 18 is suspended in 50 ml of dichloromethane. 35.4 mg of oxalyl chloride (0.279 mmol) is added, followed by 1 drop of DMF. The reaction is refluxed under nitrogen for 2 hours, and stirred at room temperature for an additional 12 hours. Then an excess amount of 0.5 M ammonia in dioxane is added. The reaction is stirred at room temperature for 1 hour. The solvent is then removed in vacuum and the residue is washed with 1:1 water:methanol to yield 70 mg of an off-white powder as the desired product.

Workup

  1. temperatureThe reaction is refluxed under nitrogen for 2 hours
  2. stirringThe reaction is stirred at room temperature for 1 hour
  3. customThe solvent is then removed in vacuum
  4. washthe residue is washed with 1:1 water

Sources & evidence

ORD record
ord-7d620b363f8946eb8675d9bf70a531d6
Source dataset
uspto-grants-2004_06
Patent number
US06747147B2

Reaction notes

Loading…